WO1995011250A1 - Procede de preparation d'ethers glyceriques d'alkyloligoglucosides et/ou d'alcenyloligoglucosides - Google Patents

Procede de preparation d'ethers glyceriques d'alkyloligoglucosides et/ou d'alcenyloligoglucosides Download PDF

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Publication number
WO1995011250A1
WO1995011250A1 PCT/EP1994/003377 EP9403377W WO9511250A1 WO 1995011250 A1 WO1995011250 A1 WO 1995011250A1 EP 9403377 W EP9403377 W EP 9403377W WO 9511250 A1 WO9511250 A1 WO 9511250A1
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Prior art keywords
alkyl
alkenyl
glycerol
carbon atoms
alcohol
Prior art date
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PCT/EP1994/003377
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German (de)
English (en)
Inventor
Manfred Weuthen
Udo Hees
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
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Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of WO1995011250A1 publication Critical patent/WO1995011250A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives

Definitions

  • the invention relates to a process for the preparation of alkyl and / or alkenyl oligoglycoside glycerol ethers, in which alkyl and / or alkenyl oligoglycosides are reacted with glycerol carbonate.
  • Alkyl oligoglycosides and in particular alkyl oligoglucosides are nonionic surfactants that are becoming increasingly important due to their natural raw material base - fatty alcohol and sugar - and are used, for example, in manual dishwashing detergents or cosmetic products [cf. Tens. Surf.Det. .28, 413 (1991)]. Nevertheless, alkyl oligoglycosides show in some applications that their foaming power is not completely satisfactory. The cold water solubility and the crystallization behavior are also in need of improvement.
  • the object of the invention was therefore to provide new nonionic derivatives of the alkyl and / or alkenyl oligoglycosides which are free from the disadvantages described.
  • the invention relates to a process for the preparation of alkyl and / or alkenyl oligoglycoside glycerol ethers, in which alkyl and / or alkenyl oligoglycosides of the formula (I)
  • R 1 is an alkyl and / or alkenyl radical having 1 to 22 carbon atoms or a glycerol, ethylene glycol, pro pylene glycol or sorbitol residue
  • G stands for a sugar with 5 or 6 carbon atoms
  • p stands for numbers from 1 to 10, with glycerol carbonate.
  • the new ethers have greater foaming power, better solubility in cold water and a reduced tendency to crystallize compared to alkyl oligoglycosides. In addition, they are well tolerated by the skin and are completely biodegradable.
  • Alkyl and alkenyl oligoglycosides are known substances which can be obtained by the relevant processes in preparative organic chemistry. Representative of the extensive literature, reference is made here to the publications EP-Al-0 301 298 and WO 90/3977.
  • the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
  • the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
  • the alkyl or alkenyl radical R 1 can be derived from primary alcohols having 1 to 11, preferably 8 to 10, carbon atoms. Typical examples are methanol, butanol, capron alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
  • the alkyl or alkenyl radical R can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol and their technical mixtures, which can be obtained as described above. Alkyl oligoglucosides based on hardened Ci2 / i4 * coconut alcohol with a DP of 1 to 3 are preferred.
  • the starting materials can also be polyoligoglycosides, preferably glycerol, ethylene glycol, propylene glycol or sorbitol oligoglucosides.
  • Glycerol carbonate is a known compound which can be prepared, for example, by reacting phosgene with glycerol or reacting glycerol, carbon monoxide and oxygen in the presence of cupfer catalysts.
  • the alkyl and / or alkenyl oligoglycosides and the glycerol carbonate can usually be used in a molar ratio of 3: 1 to 1:10. This means that the stoichiometric conversion of the reaction partners is not sought in all cases. In particular, there is an interest in mixtures in which only a certain proportion of the alkyl and / or alkenyl oligoglycosides are etherified. Conversely, an excess of glycerol carbonate is required if the reaction is to be carried out as completely as possible. However, an application ratio of 2: 1 to 1: 3 is usually recommended.
  • the acetal bond present is of course recommended to use basic catalysts, for example alkali and / or alkaline earth oxides, hydroxides, carbonates or C 1 -C 4 -alcoholates. Typical examples are sodium hydroxide, sodium hydrogen carbonate, sodium methanolate, potassium hydroxide and potassium carbonate.
  • the amount of alkaline catalysts used can be 0.5 to 5, preferably 1 to 2 mol%, based on the glycoside.
  • glycoside and glycerol carbonate are introduced, heated, an aqueous or alcoholic solution of the catalyst is added at the reaction temperature and the solvent introduced is removed, if appropriate, in vacuo.
  • the reaction is preferably carried out at temperatures in the range from 60 to 180, preferably 70 to 130 ° C; the reaction time can be between 1 and 5 hours.
  • the reaction is complete when there is no more carbon dioxide evolution.
  • the products can be dissolved in water or pasted with water and mixed in a manner known per se, e.g. B. be bleached by adding hydrogen peroxide.
  • alkyl and / or alkenyl oligoglycoside glycerol ethers according to the invention have surface-active properties. They promote the wetting of hard surfaces and the emulsification of otherwise immiscible phases.
  • the alkyl and / or alkenyl oligoglycoside glycerol ethers can therefore be used for the production of surface-active agents, in particular detergents, dishwashing detergents and cleaning agents, and products for hair and body care, in which they are present in amounts of 1 to 50, preferably 5 to 30,% by weight. - based on the funds - may be included.
  • Example 3 Analogously to Example 1, 354 g (3 mol) of glycerol carbonate were reacted with 450 g (1 mol) of hexadecyl glucoside (DP grade: 1.4) and 1 g of sodium hydrogen carbonate. The reaction temperature was 140 ° C, the reaction time 7 h and the yield 92% of theory.
  • Example 3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Saccharide Compounds (AREA)
  • Detergent Compositions (AREA)

Abstract

On obtient des éthers glycériques d'alkyloligoglucosides et/ou d'alcényloligoglucosides en faisent réagir avec du carbonate de glycérine des alkyloligoglucosides et/ou des alcényloligoglucosides de la formule (I): R1-O-[G]¿p? dans laquelle R?1¿ désigne un reste alkyle et/ou alcényle avec 1 à 22 atomes de carbone ou un reste glycérine, éthylèneglycol, propylèneglycol ou sorbitol, G un sucre avec 5 ou 6 atomes de carbone et p un nombre compris entre 1 et 10. Les produits obtenus se caractérisent par des propriétés détergentes exceptionnelles.
PCT/EP1994/003377 1993-10-21 1994-10-13 Procede de preparation d'ethers glyceriques d'alkyloligoglucosides et/ou d'alcenyloligoglucosides WO1995011250A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19934335947 DE4335947A1 (de) 1993-10-21 1993-10-21 Verfahren zur Herstellung von Alkyl- und/oder Alkenyloligoglykosidglycerinethern
DEP4335947.7 1993-10-21

Publications (1)

Publication Number Publication Date
WO1995011250A1 true WO1995011250A1 (fr) 1995-04-27

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PCT/EP1994/003377 WO1995011250A1 (fr) 1993-10-21 1994-10-13 Procede de preparation d'ethers glyceriques d'alkyloligoglucosides et/ou d'alcenyloligoglucosides

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DE (1) DE4335947A1 (fr)
WO (1) WO1995011250A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9296858B2 (en) 2011-02-22 2016-03-29 Basf Se Polymers based on glycerol carbonate and an amine
US9994674B2 (en) 2011-02-22 2018-06-12 Basf Se Polymers based on glycerol carbonate

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19737497C2 (de) * 1997-08-28 2001-02-22 Cognis Deutschland Gmbh Wäßrige Hautreinigungsmittel in Emulsionsform

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2854449A (en) * 1953-06-04 1958-09-30 Petrolite Corp Process for preparing oxyalkylated derivatives
US2854447A (en) * 1953-06-04 1958-09-30 Petrolite Corp Process for preparing oxyalkylated derivatives
US3088980A (en) * 1963-05-07 Hydroxyalkylation of phenols
US4011389A (en) * 1975-03-21 1977-03-08 Basf Wyandotte Corporation Glycoside polyethers
US4474951A (en) * 1983-09-27 1984-10-02 The Dow Chemical Company Hydroxyalkylation of polysaccharides
JPH03291296A (ja) * 1990-04-09 1991-12-20 Kao Corp ２，３―エポキシプロピル化グリコシド及びその製造中間体並びにその製造方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3088980A (en) * 1963-05-07 Hydroxyalkylation of phenols
US2854449A (en) * 1953-06-04 1958-09-30 Petrolite Corp Process for preparing oxyalkylated derivatives
US2854447A (en) * 1953-06-04 1958-09-30 Petrolite Corp Process for preparing oxyalkylated derivatives
US4011389A (en) * 1975-03-21 1977-03-08 Basf Wyandotte Corporation Glycoside polyethers
US4474951A (en) * 1983-09-27 1984-10-02 The Dow Chemical Company Hydroxyalkylation of polysaccharides
JPH03291296A (ja) * 1990-04-09 1991-12-20 Kao Corp ２，３―エポキシプロピル化グリコシド及びその製造中間体並びにその製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Derwent World Patents Index; AN 92-046009, "New 2,3-epoxy-propylated glycoside(s)" *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9296858B2 (en) 2011-02-22 2016-03-29 Basf Se Polymers based on glycerol carbonate and an amine
US9994674B2 (en) 2011-02-22 2018-06-12 Basf Se Polymers based on glycerol carbonate

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Publication number Publication date
DE4335947A1 (de) 1995-04-27

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